WO2016146685A1 - Silane und härtbare zusammensetzungen, die diese silane als vernetzer enthalten - Google Patents

Silane und härtbare zusammensetzungen, die diese silane als vernetzer enthalten Download PDF

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Publication number
WO2016146685A1
WO2016146685A1 PCT/EP2016/055693 EP2016055693W WO2016146685A1 WO 2016146685 A1 WO2016146685 A1 WO 2016146685A1 EP 2016055693 W EP2016055693 W EP 2016055693W WO 2016146685 A1 WO2016146685 A1 WO 2016146685A1
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radical
substituted
independently
unsubstituted alkyl
formula
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PCT/EP2016/055693
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German (de)
English (en)
French (fr)
Inventor
Andrea GUTACKER
Johann Klein
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Henkel Ag & Co. Kgaa
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Priority to BR112017019626-3A priority Critical patent/BR112017019626B1/pt
Priority to CN201680016133.5A priority patent/CN107428785B/zh
Priority to CA2979928A priority patent/CA2979928C/en
Priority to KR1020177029646A priority patent/KR102572117B1/ko
Priority to PL16711802T priority patent/PL3271367T3/pl
Priority to JP2017549078A priority patent/JP6688313B2/ja
Application filed by Henkel Ag & Co. Kgaa filed Critical Henkel Ag & Co. Kgaa
Priority to MX2017011821A priority patent/MX2017011821A/es
Priority to ES16711802T priority patent/ES2717522T3/es
Priority to EP16711802.5A priority patent/EP3271367B1/de
Priority to RU2017134289A priority patent/RU2711919C2/ru
Publication of WO2016146685A1 publication Critical patent/WO2016146685A1/de
Priority to US15/702,820 priority patent/US10487096B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5455—Silicon-containing compounds containing nitrogen containing at least one group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C08K5/57—Organo-tin compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups

Definitions

  • the invention relates to new silanes containing at least one particular a-hydroxycarboxylic acid amide residue, their preparation, and curable compositions containing the silane and a curable polyorganosiloxane.
  • the silane acts as a crosslinker in the curable compositions and is characterized in particular by excellent stability even after prolonged storage in admixture with conventional further constituents of curable compositions.
  • Silicone polymers are of great importance in the production of adhesives, sealants, coatings and insulating materials. Among them, those which vulcanize at low temperatures and under ambient conditions make up a not inconsiderable market share.
  • Typical formulations contain a reactive polyorganosiloxane. This is usually a silanol-terminated polyorganosiloxane, wherein the polyorganosiloxane has at least one, preferably two, attached to a silicon atom hydroxy groups. This is used in combination with a silane-based crosslinker having hydrolyzable groups attached to the silicon atom.
  • crosslinker is sometimes spoken of hardener.
  • crosslinker and hardener are synonymous.
  • the polyorganosiloxane and the crosslinker may be present as separate components. Often, however, the polyorganosiloxane is selectively reacted with the crosslinker to form a modified polyorganosiloxane, and this modified polyorganosiloxane is added to the curable composition.
  • endcapping endcapping
  • crosslinkers There are numerous crosslinkers known for silicone systems. These can be differentiated from the liberated on hydrolysis leaving groups into acidic, basic and neutral crosslinked. Typical acidic crosslinkers contain acid groups as hydrolyzable groups and release the corresponding acids, eg acetic acid, upon crosslinking. Typical basic crosslinkers release amines on crosslinking. In both cases, aggressive compounds are released during crosslinking, which can corrode or decompose, for example, metals, stone or mortar, and which also have an intensive, often unpleasant odor. Therefore, neutral curatives are often used for modern curable silicone compositions. Typical representatives of neutral crosslinkers have hydrolyzable groups which split off alcohol or oxime on crosslinking.
  • Oximosilane crosslinkers which hydrolyze with the release of an alkanone oxime, generally do not have these disadvantages and are therefore frequently used.
  • the most common representative of oximosilane crosslinkers releases butane-2-onoxime upon crosslinking. This is suspected to cause cancer, so there is an urgent need for alternative neutral crosslinkers.
  • the released oximes also have an intense, foul odor and working with curable compositions containing a corresponding crosslinker is perceived by the users as unpleasant.
  • Silane compounds have therefore already been proposed as alternative crosslinkers which release ⁇ -hydroxycarboxylic acid esters or ⁇ -hydroxycarboxamides on crosslinking.
  • silane compounds have long been known and described, for example, by M. M. Sprung in "Some ⁇ -Carbalkoxyalkoxysilanes", J. Org. Chem., 1958, 23 (10), pages 1530-1534.
  • DE 32 10 337 A1 also discloses corresponding silane compounds, their preparation and use in curable compositions based on polydiorganosiloxanes which have condensable end groups.
  • EP 2 030 976 A1 discloses hardeners for silicone rubber compositions which contain three 2-hydroxypropionic acid alkyl ester residues, i. Lactic acid alkyl ester residues. Particularly preferred is the vinyl tris (ethyl lacto) silane.
  • EP 2 774 672 A1 describes special catalysts for the crosslinking of silicone rubber compositions with a crosslinker based on a silane compound with lactate groups.
  • the crosslinker may in turn be the compounds known from EP 2 030 976 A1.
  • crosslinkers are disclosed which have only one, two or even four 2-Hydroxyproprionklarealkylester radicals.
  • crosslinking agent based on a silane compound with lactate groups or similar ⁇ -carbalkoxyalkoxy groups brings many advantages, these crosslinkers have not been able to establish themselves in practice. This is particularly due to the difficulty of formulating silicone-based curable compositions containing these crosslinkers so as to provide adequate storage stability. Especially in the presence of other customary and often indispensable constituents of such compositions, in particular of curing catalysts and adhesion promoters, the stability of the silane compound and thus the storage stability of the curable compositions suffer drastically. It is therefore an object of the present invention to provide novel silane compounds which can be used as neutral crosslinkers in curable compositions based on polyorganosiloxanes without adversely affecting the storage stability of the curable compositions.
  • the present invention achieves the object by providing the silane compounds according to the invention which have at least one particular ⁇ -hydroxycarboxylic acid amide radical.
  • the invention therefore provides silanes of the formula (1)
  • each R 2 is independently a radical of general formula (2):
  • each R 4 is independently:
  • R 5 stands for:
  • R 5 2 stands for:
  • R 5 3 stands for:
  • each R 3 is independently a radical of general formula (3):
  • each R 6 is independently:
  • R 7 stands for:
  • a radical - (CH 2) q -COOR 9 wherein p is an integer from 2 to 10, in particular 2 and R 9 is a substituted or unsubstituted alkyl, alkenyl or alkynyl radical, or a substituted or unsubstituted cycloaliphatic radical or aryl radical ;
  • R 8 is a radical of the general formula (4):
  • R 0 stands for:
  • each R is independently:
  • each R 2 is independently: a substituted or unsubstituted alkyl, alkenyl or alkynyl radical,
  • each R 3 is independently:
  • R 4 stands for:
  • n + m a substituted or unsubstituted alkyl, alkenyl or alkynyl radical; and o is independently 0, 1 or 2 and m is independently 0 or 1 and n is independently 0, 1, 2 or 3, the sum of n + m being at most 3.
  • Another object of the invention is a process for preparing the silanes of the invention.
  • the invention further relates to curable compositions comprising at least one silane according to the invention and at least one polyorganosiloxane, wherein the polyorganosiloxane has at least one hydroxyl group bonded to a silicon atom.
  • curable composition is understood to mean a substance or a mixture of several substances which is curable by physical or chemical measures, whereby these chemical or physical measures can be, for example, the supply of energy in the form of heat, light or other electromagnetic Radiation, but also in the most simple contact with atmospheric moisture, water or a reactive component, the composition goes from the initial state in a state that has higher hardness.
  • the weight average refers to molecular weights of oligomers or polymers.
  • the molecular weight is determined by means of gel permeation chromatography (GPC) with tetrahydrofuran (THF) as the eluant according to DIN 55672-1: 2007-08, preferably at 35 ° C.
  • GPC gel permeation chromatography
  • THF tetrahydrofuran
  • Molecular weights of monomers Compounds are calculated on the basis of the respective empirical formula and the known molecular weights of the individual atoms.
  • At least one as used herein means 1 or more, ie 1, 2, 3, 4, 5, 6, 7, 8, 9 or more. With respect to an ingredient, the indication refers to the kind of the ingredient and not to the absolute number of molecules. "At least one polymer” thus means, for example, at least one type of polymer, ie that one type of polymer or a mixture of several different polymers can be used. The term, together with weights, refers to all compounds of the type indicated which are included in the composition / mixture, i. that the composition does not contain any further compounds of this type beyond the stated amount of the corresponding compounds.
  • Alkyl refers to a saturated aliphatic hydrocarbon including straight chain and branched chain groups
  • the alkyl group has from 1 to 10 carbon atoms (when a numerical range eg "1-10" is given herein, it is meant that this group
  • the alkyl group may have the alkyl group, 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc.
  • the alkyl may be a middle alkyl having 5 to 6 carbon atoms or a lower alkyl 1 to 4 carbon atoms have, for example, methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, tert-butyl, etc.
  • the substituted or unsubstituted alkyl radicals may be "substituted" as used in this context, in that one or more carbon atoms and / or hydrogen atoms of the alkyl radical are replaced by heteroatoms or functional groups.
  • heteroalkyl groups are obtained in which one or more carbon atoms are replaced by heteroatoms, in particular selected from O, S, N and Si.
  • heteroalkyl groups include, without limitation, methoxymethyl, ethoxyethyl, propoxypropyl, methoxyethyl, isopentoxypropyl, ethylaminoethyl, tnmethoxypropylsilyl, etc.
  • Alkenyl refers to an alkyl group as defined herein which consists of at least two carbon atoms and at least one carbon-carbon double bond, for example ethenyl, propenyl, butenyl or pentenyl and their structural isomers such as 1- or 2 Propenyl, 1-, 2-, or 3-butenyl, etc.
  • Alkenyl groups may be substituted or unsubstituted, and when substituted, the substituents are as defined above for alkyl.
  • Alkynyl refers to an alkyl group as defined herein which consists of at least two carbon atoms and at least one carbon-carbon triple bond, e.g., ethynyl (acetylene), propynyl, butynyl, or petinyl and their structural Isomers as described above Alkynyl groups may be substituted or unsubstituted, and when substituted, the substituents are as defined above for alkyl.
  • cycloaliphatic radical or "cycloalkyl group” as used herein refers to monocyclic or polycyclic (multiple rings having common carbon atoms) groups, especially from 3-8 carbon atoms, in which the ring does not have a complete conjugated pi-electron system. for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, etc. Cycloalkyl groups may be substituted or unsubstituted.
  • Aryl refers to monocyclic or polycyclic (ie, rings having adjacent carbon atoms) groups, especially from 6 to 14 carbon ring atoms, having a complete conjugated pi-electron system.
  • aryl groups are phenyl, naphthalenyl, and anthracenyl
  • Aryl groups may be substituted or unsubstituted, and when substituted, the substituents are as defined above for cycloalkyl.
  • heteroaryl group refers to a monocyclic or polycyclic (ie, rings sharing an adjacent ring atomic pair) aromatic ring, especially 5 to 10 ring atoms, where one, two, three or four ring atoms are nitrogen,
  • heteroaryl groups are pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 1,2,3- Triazolyl, 1, 2,4-triazolyl, 1, 2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 3,4-triazinyl, 1, 2,3-triazinyl, benzofuryl, isobenzofuryl, benzothienyl, benzotriazolyl, isobenzothienyl, isobenzothienyl
  • heteroalicyclic radical or a “heterocycloalkyl group” as used herein refers to a monocyclic or fused ring of 5 to 10 ring atoms containing one, two or three heteroatoms selected from N, O and S, wherein the The rest of the ring atoms is carbon.
  • heterocycloalkenyl group additionally contains one or more double bonds, but the ring does not have a complete conjugated pi-electron system
  • heteroalicyclic groups are pyrrolidine, piperidine, piperazine, morpholine, imidazolidine, tetrahydropyridazine, tetrahydrofuran, thiomorpholine, tetrahydropyridine, and the like.
  • Heterocycloalkyl groups may be substituted or unsubstituted, and when substituted, the substituents are as defined above for cycloalkyl.
  • silanes according to the invention are silanes of the formula (1):
  • Each R independently represents a substituted or unsubstituted alkyl, alkenyl or alkynyl radical; a substituted or unsubstituted cycloaliphatic radical or aryl radical; or a substituted or unsubstituted heteroalicyclic radical or heteroaryl radical.
  • each R is independently an alkyl radical of 1 to 10 carbon atoms, preferably of 1 to 4 carbon atoms, especially methyl, ethyl, propyl or isopropyl, an alkenyl radical of 2 to 10 carbon atoms, preferably 2 to 4 carbon atoms, especially vinyl or allyl , or an aryl radical having 6 to 10 carbon atoms, in particular phenyl.
  • R particularly independently of one another is methyl, vinyl or phenyl, very particularly preferably methyl or vinyl.
  • each R 2 is independently a radical of general formula (2): -OCR 4 2 COOR 5 (2), where
  • each R 4 is independently:
  • R 5 stands for:
  • R 5 2 stands for:
  • R 5 3 stands for:
  • R 2 is an ⁇ -hydroxycarboxylic acid ester radical, an alkoxy radical or an acyloxy radical.
  • each R 2 is independently a radical of formula (2) wherein one of R 4 is hydrogen and the second of R 4 is hydrogen or a substituted or unsubstituted alkyl radical of 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical 1 to 10 carbon atoms, preferably having 1 to 4 carbon atoms, in particular methyl, and / or, preferably and, R 5 represents a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably methyl or ethyl. More preferably, each R 2 is independently a radical of formula (2) wherein one of R 4 is hydrogen and the second of R 4 is methyl and R 5 is ethyl.
  • At least one R 2 is a radical of formula (2-2) or a radical of formula (2-3), preferably a radical of formula (2-2).
  • R 5 2 and R 5 3 are each preferably a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, in particular having 1 to 4 carbon atoms, particularly preferably methyl or ethyl.
  • each R 2 is independently a radical of formula (2-2), wherein R 5 2 is a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, especially 1 to 4 carbon atoms, more preferably methyl or Ethyl, stands.
  • each R 3 is independently a radical of general formula (3):
  • R 3 is an ⁇ -hydroxycarboxylic acid amide residue.
  • Each R 6 is independently:
  • R 7 stands for:
  • a radical - (CH 2) q -COOR 9 wherein p is an integer from 2 to 10, in particular 2 and R 9 is a substituted or unsubstituted alkyl, alkenyl or alkynyl radical, or a substituted or unsubstituted cycloaliphatic radical or aryl radical ;
  • R 8 is a radical of the general formula (4):
  • R 0 stands for:
  • R independently stands for: a substituted or unsubstituted alkyl, alkenyl or alkynyl radical;
  • each R 2 is independently:
  • each R 3 is independently:
  • R 4 stands for:
  • n + m a substituted or unsubstituted alkyl, alkenyl or alkynyl radical; and o is independently 0, 1 or 2 and m is independently 0 or 1 and n is independently 0, 1, 2 or 3, the sum of n + m being at most 3.
  • one of R 6 is hydrogen and the second R 6 is hydrogen or a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, especially methyl.
  • R 7 is preferably hydrogen, a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, in particular having 1 to 4 carbon atoms, in particular methyl, or R 8 .
  • R 0 is preferably an alkylene radical of the formula - (CH 2) P -, where p is an integer from 1 to 6, in particular 3.
  • Each R is preferably independently of one another a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, in particular having 1 to 4 carbon atoms, more preferably methyl or ethyl.
  • Each R 2 is preferably independently a substituted or unsubstituted alkyl radical of 1 to 10 carbon atoms, preferably an unsubstituted one Alkyl radical having 1 to 10 carbon atoms, in particular having 1 to 4 carbon atoms, more preferably methyl or ethyl.
  • Each R 3 is preferably hydrogen or a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, especially methyl.
  • one radical R 3 is hydrogen and the second of the radicals R 3 is hydrogen or a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, in particular methyl.
  • R 4 preferably represents a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably methyl or ethyl.
  • o is 0, 1 or 2, preferably 0 or 1, more preferably 0.
  • each R 3 is independently a radical of formula (3) wherein one of R 6 is hydrogen and the second of R 6 is hydrogen or a substituted or unsubstituted alkyl radical of 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical 1 to 10 carbon atoms, preferably having 1 to 4 carbon atoms, in particular methyl, R 7 is hydrogen, a substituted or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atoms, in particular having 1 to 4 carbon atoms, in particular methyl and R 8 is a radical of the formula (4) wherein R 0 is an alkylene radical of the formula - (CH 2) P -, where p is an integer from 1 to 6, especially 3, each R is independently a substituted one or unsubstituted alkyl radical having 1 to 10 carbon atoms, preferably an unsubstituted alkyl radical having 1 to 10 carbon atom
  • each R 3 is independently a radical of formula (3), wherein one of R 6 is hydrogen and the second of R 6 is methyl, R 7 is hydrogen or methyl, and R 8 is a radical of formula (4) wherein R 0 is an alkylene radical of the formula - (CH 2) p - wherein p is 3, each R is independently methyl or ethyl, and each R 2 independently of one another is methyl or ethyl, and o is 0, 1 or 2, preferably 0 or 1, particularly preferably 0.
  • n and m are chosen such that the sum of n + m is at most 3, ie the silane of the formula (1) contains at least one radical R 3 , ie at least one o-hydroxycarboxylic acid amide radical.
  • n stands for 0 or 1, preferably for 1.
  • m stands for 0, 1, 2 or 3, preferably for 0, 1 or 2, particularly preferably for 2.
  • Very particularly preferred silanes of the formula (1) are selected from compounds which are obtained by targeted amidation of methyltris (ethyllactato) silane, ethyltris (ethyllactato) silane, phenyltris (ethyllactato) silane, vinyltris (ethyllactato) silane , Tetra (ethyllactato) silane or mixtures thereof with an amine of the formula (6):
  • R 7 , R 0 , and each R and each R 2 each independently, have the general, preferred and particularly preferred meanings given above. It is particularly preferably an amidation product of methyltris (ethyllactato) silane, ethyltris (ethyllactato) silane, phenyltris (ethyllactato) silane, vinyltris (ethyllactato) silane,
  • the invention furthermore relates to a process for preparing the silanes according to the invention, where a silane of the formula (5) in which
  • each R and each R 2 each independently, have the general, preferred and particularly preferred meanings given above, with at least one aminosilane compound of the general formula (6):
  • the molar ratio of silane of the formula (5) to the aminosilane compound of the general formula (6) is preferably 2: 1 to 30: 1, more preferably 4: 1 to 15: 1.
  • the silane of the formula (5) and the aminosilane compound of the general formula (6) are reacted at normal pressure (1 bar) and at a temperature of 40 to 80 ° C, preferably 50 to 80 ° C, particularly preferably 60 to 80 ° C.
  • the starting materials mentioned are stirred together, preferably for at least 10 minutes, preferably at least 30 minutes, more preferably at least 60 minutes.
  • the invention furthermore relates to curable compositions comprising at least one silane of the formula (1) and at least one polyorganosiloxane, where the polyorganosiloxane has at least one hydroxyl group bonded to a silicon atom.
  • the curable compositions contain the silane of the formula (1) preferably in an amount of 2 to 7 wt .-%, particularly preferably in an amount of 4 to 6 wt .-%, each based on the total weight of the composition. If a mixture of several silanes of the formula (1) is used, the amounts given are of course based on the total amount of silanes of the formula (1) in the composition.
  • the curable compositions also contain at least one polyorganosiloxane having at least one hydroxyl group attached to a silicon atom.
  • the polyorganosiloxane has at least two hydroxyl groups bonded to a silicon atom. It is also preferred that the hydroxy group or hydroxy groups are attached to terminal silicon atoms. If the polyorganosiloxane is branched, it preferably has a hydroxy group at each end.
  • the polyorganosiloxane having at least one hydroxyl group bonded to a silicon atom is a polydiorganosiloxane, preferably a polydimethylsiloxane.
  • an ⁇ , ⁇ -dihydroxy-terminated polydiorganosiloxane especially an ⁇ , ⁇ -dihydroxy-terminated polydimethylsiloxane
  • ⁇ , ⁇ -dihydroxy-terminated polydimethylsiloxanes which have a kinematic viscosity 25 ° C from 5000 to 120000 cSt, in particular 10,000 to 100,000 cSt and more preferably 50,000 to 90,000 cSt.
  • the curable compositions contain the at least one polyorganosiloxane having at least one hydroxyl group bonded to a silicon atom, preferably in an amount of from 30 to 90% by weight, more preferably in an amount of from 40 to 60% by weight, based in each case the total weight of the composition.
  • the amounts given refer to the total amount of polyorganosiloxanes having at least one hydroxyl group attached to a silicon atom in the composition.
  • the curable compositions may contain the polyorganosiloxane having at least one hydroxy group bonded to a silicon atom and the silane of formula (1) as separate components. However, it is also possible that these components are in the form of a prepolymer.
  • the prepolymer is a reaction product of the two components.
  • Corresponding implementations are known and are also referred to as endcapping. This may optionally be carried out in the presence of a catalyst, which should selectively mediate the End disabilityverkappung without simultaneously curing the polyorganosiloxane.
  • Suitable catalysts are, for example, acids, organic lithium compounds, as described, for example, in EP 0 564 253 A1, amines, inorganic oxides, potassium acetate, organotitanium derivatives, titanium / amine combinations and carboxylic acid / amine combinations.
  • the abovementioned amounts for polyorganosiloxane on the one hand and silane on the other hand for the prepolymer additively are present, then the abovementioned amounts for polyorganosiloxane on the one hand and silane on the other hand for the prepolymer additively.
  • the curable compositions thus preferably contain the prepolymer in an amount of from 32 to 97% by weight, more preferably in an amount of from 44 to 66% by weight, based in each case on the total weight of the composition. Of course, if a mixture of several prepolymers is used, the amounts given are based on the total amount of prepolymers in the composition.
  • compositions of the invention crosslink in the presence of moisture and thereby cure to form Si-O-Si bonds. This curing can be accelerated by adding a suitable curing catalyst.
  • the curable composition therefore preferably also comprises at least one curing catalyst, in particular a tin compound.
  • a tin compound Preferably, it is an organotin compound or an inorganic tin salt. Tin is preferably present in these tin compounds in di- or tetravalent form.
  • Suitable inorganic tin salts are, for example, tin (II) chloride and tin (IV) chloride.
  • organotin compounds tin organyls
  • tin organyls are preferably used as tin compounds.
  • organotin compounds are the 1,3-dicarbonyl compounds of di- or tetravalent tin, for example the acetylacetonates such as di (n-butyl) tin (IV) di (acetylacetonate), di (n-octyl) tin (IV ) -di (acetylacetonate), (n-octyl) (n-butyl) -tin (IV) di (acetylacetonate); the dialkyltin (IV) -dicarboxylates, for example di-n-butyltin dilaurate, di-n-butyltin maleate, di-n-butyltin diacetate, di-n-octyltin dilaurate, di-n-octyltin diacetate or the corresponding dialkoxylates, for example di-n- butylzinndimethoxid; Oxides of tetrafluor
  • tin compounds of ethyl silicate dimethyl maleate, diethyl maleate, dioctyl maleate, dimethyl phthalate, diethyl phthalate, dioctyl phthalate
  • the tin compound is selected from 1,3-dicarbonyl compounds of the di- or tetravalent tin, the dialkyltin (IV) -dicarboxylates, the dialkyltin (IV) dialkoxylates, the dialkyltin (IV) oxides, the tin ( ll) -carboxylates and mixtures thereof.
  • the tin compound is particularly preferably a dialkyltin (IV) -dicarboxylate, in particular di-n-butyltin dilaurate or di-n-octyltin dilaurate.
  • tin-free curing catalysts can be used. Although the tin compounds show very high catalytic activity, they are sometimes suspected of being hazardous to health. In a particular embodiment, therefore, the compositions contain exclusively tin-free curing catalysts, ie are tin-free.
  • Suitable tin-free curing catalysts are, for example, organometallic compounds of iron, in particular the 1, 3-dicarbonyl compounds of iron such. For example, iron (III) acetylacetonate.
  • Boron halides such as boron trifluoride, boron trichloride, boron tribromide, boron triiodide or mixed boron halides can also be used as curing catalysts.
  • Particularly preferred are boron trifluoride complexes such as e.g. Bortrifluorid diethyletherat, which are easier to handle as liquids than gaseous boron halides.
  • amines, nitrogen heterocycles and guanidine derivatives are generally suitable for catalysis.
  • a particularly suitable catalyst from this group is 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU).
  • titanium, aluminum and zirconium compounds or mixtures of one or more catalysts of one or more of the groups just mentioned are preferably used as catalysts.
  • the use of tin compounds can be avoided in this way, on the other hand, a better adhesion to normally poorly adhering organic surfaces such. B. reach acrylates.
  • the titanium catalysts are preferably used because they provide the best curing results.
  • Titanium catalysts are compounds which have hydroxyl groups and / or substituted or unsubstituted alkoxy groups, ie titanium alkoxides of the general formula
  • R z is an organic group, preferably a substituted or unsubstituted hydrocarbon group having 1 to 20 C atoms, and the 4 alkoxy groups -OR z are the same or different. Furthermore, one or more of the radicals -OR z can be replaced by acyloxy groups -OCOR z .
  • titanium catalysts titanium alkoxides in which one or more alkoxy groups are replaced by a hydroxyl group or halogen atoms.
  • titanium chelate complexes can be used.
  • Aluminum catalysts can also be used as curing catalysts,
  • R z has the above meaning, ie an organic group, preferably a substituted or unsubstituted hydrocarbon radical having 1 to 20 C atoms and the three radicals R z are identical or different.
  • R z has the above meaning, ie an organic group, preferably a substituted or unsubstituted hydrocarbon radical having 1 to 20 C atoms and the three radicals R z are identical or different.
  • one or more of the alkoxy radicals may be replaced by acyloxy radicals -OC (O) R z .
  • the pure aluminum alcoholates are preferred in view of their stability to moisture and the hardenability of the mixtures to which they are added.
  • aluminum chelate complexes are preferred.
  • Suitable zirconium catalysts are, for example: tetramethoxyzirconium, tetraethoxyzirconium.
  • diisopropoxyzirconium bis ethylacetoacetate
  • triisopropoxyzirconium ethylacetoacetate
  • isopropoxyzircontris ethylacetoacetate
  • zirconacylates for example, can be used.
  • Halogenated zirconium catalysts can also be used.
  • zirconium chelate complexes can also be used.
  • carboxylic acid salts of metals can be used as curing catalysts carboxylic acid salts of metals or a mixture of several such salts, these being selected from the carboxylates of the following metals: calcium, vanadium, iron, zinc, titanium, potassium, barium, manganese, nickel, cobalt and / or zirconium ,
  • the calcium, vanadium, iron, zinc, titanium, potassium, barium, manganese and zirconium carboxylates are preferred because of their high activity. Particularly preferred are calcium, vanadium, iron, zinc, titanium and Zirkoniumcarboxylate. Very particular preference is given to iron and titanium carboxylates.
  • the curable compositions contain the curing catalyst preferably in an amount of 0.01 to 2 wt .-%, preferably in an amount of 0.05 to 2 wt .-%, particularly preferably in an amount of 0.1 to 0.5 wt .-%, each based on the total weight of the composition. Of course, if a mixture of several curing catalysts is used, the amounts will refer to the total amount of cure catalyst in the composition.
  • the curable compositions may contain, in addition to the constituents already mentioned, one or more further constituents which may serve to specifically influence certain properties of the curable composition and / or of the cured product.
  • these further constituents may be selected, for example, from the group comprising plasticizers, stabilizers, antioxidants, fillers, reactive diluents, drying agents, adhesion promoters, UV stabilizers, rheological auxiliaries and / or solvents.
  • plasticizers stabilizers, antioxidants, fillers, reactive diluents, drying agents, adhesion promoters, UV stabilizers, rheological auxiliaries and / or solvents.
  • adhesion promoters, plasticizers, fillers and stabilizers, including antioxidants and UV stabilizers are of particular importance.
  • the curable compositions therefore preferably contain at least one further constituent.
  • the curable composition according to the invention may accordingly also contain one or more adhesion promoters.
  • An adhesion promoter is understood as meaning a substance which improves the adhesive properties of adhesive layers on surfaces.
  • adhesion promoters Conventional adhesion promoters (tackifiers) known to the person skilled in the art can be used alone or as a combination of several compounds.
  • resins, terpene oligomers, coumarone / indene resins, aliphatic, petrochemical resins, and modified phenolic resins are suitable.
  • Hydrocarbon resins, for example, which are obtained by polymerization of terpenes, mainly o or ⁇ -pinene, dipentene or limonene, are suitable for the purposes of the present invention. The polymerization of these monomers is usually cationic with initiation with Friedel-Crafts catalysts.
  • the terpene resins also include copolymers of terpenes and other monomers, for example styrene, methylstyrene, isoprene and the like.
  • the resins mentioned are used, for example, as adhesion promoters for pressure-sensitive adhesives and coating materials.
  • the terpene-phenolic resins prepared by acid catalyzed addition of phenols to terpene or rosin.
  • Terpene phenolic resins are soluble in most organic solvents and oils and are miscible with other resins, waxes and rubbers.
  • Adhesion promoters in the abovementioned sense are suitable rosin resins and their derivatives, for example their esters or alcohols.
  • silane coupling agents in particular alkoxysilanes, with a (further) functional group such. an amino group, a mercapto group, an epoxy group, a carboxyl group, a vinyl group, an isocyanate group, an isocyanurate group or a halogen.
  • a (further) functional group such. an amino group, a mercapto group, an epoxy group, a carboxyl group, a vinyl group, an isocyanate group, an isocyanurate group or a halogen.
  • Examples are ⁇ -mercaptopropyltrimethoxysilane, ⁇ -mercaptopropyltriethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -carboxyethyltriethoxysilane, ⁇ -carboxyethylphenylbis (2-methoxyethoxy) silane, N- ⁇ - (carboxymethyl) aminoethyl - ⁇ -aminopropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, ⁇ -acroyloxypropylmethyltriethoxysilane, ⁇ -isocyanatopropyltrimethoxysilane, ⁇ -isocyanatopropyl
  • adhesion promoters are, in particular, aminosilanes (amino-functional alkoxysilanes or aminoalkylalkoxysilanes), such as, for example, ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltriisopropoxysilane, ⁇ -aminopropylmethyldimethoxysilane, ⁇ -aminopropylmethyldiethoxysilane, Y- (2-aminoethyl) -3-aminopropyltrimethoxysilane, ⁇ - (2-aminoethyl) aminopropylmethyldimethoxysilane, Y- (2-aminoethyl) aminopropyltriethoxysilane, ⁇ - (2-aminoethyl) aminopropylmethyldiethoxysilane, Y- (2-aminoeththyl
  • a coupling agent is a silane of the general formula (7)
  • R 3 and R 4 independently of one another are hydrogen or C 1 -C 5 -alkyl radicals
  • R ' is a divalent, optionally containing a heteroatom, hydrocarbon radical with
  • Ci - Cs - alkyl, Ci - Cs - alkoxy or Ci - Cs - Acyloxyreste wherein at least one of the radicals a Ci - Cs - alkoxy or Ci - Cs - Acyloxyrest or . group is.
  • such compounds have a high affinity for the binding polymer components of the curable composition according to the invention, but also for a wide range of polar and non-polar surfaces, and therefore contribute to the formation of a particularly stable adhesion between the adhesive or sealant composition and the adhesive or bonding agent to be bonded To be sealed substrates.
  • the linking group R ' may be, for example, a straight-chain or branched or cyclic, substituted or unsubstituted alkylene radical.
  • the hydrocarbon radical may be saturated or unsaturated.
  • the heteroatom contained therein is nitrogen (N) or oxygen (O).
  • R ' is preferably a hydrocarbon radical having 1 to 6 C atoms, in particular having 1 to 3 C atoms, for example methylene or n-propylene.
  • X ' , Y ' and Z ' are each independently a methyl, an ethyl, a methoxy or an ethoxy group.
  • X ' , Y ' and Z ' are particularly preferably alkoxy groups, in particular methoxy groups.
  • the group -SiX ' Y ' Z ' is a trimethoxy or dimethoxymethyl-silyl group.
  • X ' , Y ' and / or Z 'are an acyloxy group this can be done e.g. For example, be the acetoxy group -OCO-CH3.
  • An adhesion promoter which is particularly preferably used is an aminosilane compound of the general formula (6), as described above. This can therefore be used both for the preparation of the silane of formula (1), as well as assume the function of a coupling agent in the curable composition.
  • the curable compositions preferably contain the coupling agent in an amount of up to 20% by weight, preferably in an amount of 0.05 to 4% by weight, preferably in an amount of 0.1 to 2% by weight, especially preferably in an amount of 0.2 to 2 wt .-%, each based on the total weight of the composition.
  • the amounts given relate to the total amount of adhesion promoters in the composition.
  • the viscosity of the curable composition is too high for certain applications. These can then be reduced by using a reactive diluent in a simple and expedient manner, without there being any demixing phenomena (for example plasticizer migration) in the hardened mass.
  • the reactive diluent preferably has at least one functional group which, for example, reacts after application with moisture or atmospheric oxygen.
  • functional groups are Silyl groups, isocyanate groups, vinylically unsaturated groups and polyunsaturated systems.
  • Reactive diluents may be any compounds which are miscible with the other ingredients to reduce viscosity and have at least one polymer reactive group.
  • the viscosity of the reactive diluent is preferably less than 20,000 mPas, more preferably about 0, 1-6,000 mPas, most preferably 1-1,000 mPas (Brookfield RVT, 23 ° C, spindle 7, 10 U / min).
  • a reactive diluent e.g. use the following substances: polyalkylene glycols reacted with isocyanatosilanes (eg Synalox 100-50B, DOW), carbamatopropyltrimethoxysilane, alkyltrimethoxysilane, alkyltriethoxysilane, such as methyltrimethoxysilane, methyltriethoxysilane and vinyltrimethoxysilane (XL 10, Wacker), vinyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, octyltrimethoxysilane, tetraethoxysilane, vinyldimethoxymethylsilane (XL12 , Wacker), vinyltriethoxysilane (GF56, Wacker), vinyltriacetoxysilane (GF62, Wacker), isooctyltrimethoxysilane (IOtrimethoxy), is
  • polymers are also available from Kaneka Corp. can be used as reactive diluent: MS S203H, MS S303H, MS SAT 010, and MS SAX 350.
  • silane-modified polyethers e.g. derived from the reaction of isocyanatosilane with Synalox types.
  • reactive diluents polymers which can be prepared from an organic skeleton by grafting with a vinyl silane or by reacting polyol, polyisocyanate and alkoxysilane.
  • a polyol is understood as meaning a compound which may contain one or more OH groups in the molecule.
  • the OH groups can be both primary and secondary.
  • Suitable aliphatic alcohols include, for example, ethylene glycol, propylene glycol and higher glycols, as well as other polyfunctional alcohols.
  • the polyols may additionally contain other functional groups such as esters, carbonates, amides.
  • the corresponding polyol component is reacted in each case with an at least difunctional isocyanate.
  • any isocyanate having at least two isocyanate groups is suitable as the at least difunctional isocyanate, but as a rule compounds having two to four isocyanate groups, in particular two isocyanate groups, are preferred within the scope of the present invention.
  • the compound present as reactive diluent preferably has at least one alkoxysilyl group, of which the di- and trialkoxysilyl groups are preferred among the alkoxysilyl groups.
  • Suitable polyisocyanates for preparing a reactive diluent are, for example, ethylenediisocyanate, 1,4-tetramethylene diisocyanate, 1,4-tetramethoxybutane diisocyanate, 1,6-hexamethylene diisocyanate (HDI), cyclobutane-1,3-diisocyanate, cyclohexane-1, 3.
  • polyisocyanates are trihydric or higher isocyanates, as obtainable, for example, by oligomerization of diisocyanates, in particular by oligomerization of the abovementioned isocyanates.
  • trihydric and higher polyisocyanates are the triisocyanurates of HDI or IPDI or mixtures thereof or their mixed triisocyanurates and polyphenylmethylene polyisocyanate, as obtainable by phosgenation of aniline-formaldehyde condensation products.
  • solvents and / or plasticizers to reduce the viscosity of the curable composition.
  • Suitable solvents are aliphatic or aromatic hydrocarbons, halogenated hydrocarbons, ketones, ethers, esters, ester alcohols, ketoalcohols, keto ethers, ketoesters and ether esters.
  • composition described herein may further contain hydrophilic plasticizers. These serve to improve the moisture absorption and thus to improve the reactivity at low temperatures.
  • Suitable plasticizers are, for example, esters of abietic acid, adipic esters, azelaic acid esters, benzoic acid esters, butyric acid esters, acetic acid esters, esters of higher fatty acids having about 8 to about 44 carbon atoms, epoxidized fatty acids, fatty acid esters and fats, glycolic esters, phosphoric esters, phthalic acid esters, from 1 to 12 ° C -Atomen containing linear or branched alcohols, propionic acid esters, sebacic acid esters, sulfonic acid esters, thiobutyric acid esters, trimellitic acid esters, citric acid esters and esters based on nitrocellulose and polyvinyl acetate, and mixtures of two or more thereof.
  • dioctyl phthalate dibutyl phthalate, diisoundecyl phthalate or butyl benzyl phthalate
  • adipates dioctyl adipate, diisodecyl adipate, diisodecyl succinate, dibutyl sebacate or butyl oleate.
  • plasticizers are the pure or mixed ethers of monofunctional, linear or branched C 4-16 -alcohols or mixtures of two or more different ethers of such alcohols, for example dioctyl ether (available as Cetiol OE, Cognis Deutschland GmbH, Dusseldorf).
  • plasticizers are end-capped polyethylene glycols.
  • polyethylene or polypropylene glycol di-d ⁇ alkyl ethers in particular the dimethyl or diethyl ether of diethylene glycol or dipropylene glycol, and mixtures of two or more thereof.
  • plasticizers are end-capped polyethylene glycols, such as polyethylene or polypropylene glycol dialkyl ethers, where the alkyl radical is one to four C atoms, and in particular the dimethyl and diethyl ethers of diethylene glycol and dipropylene glycol. Especially with dimethyldiethylene glycol, an acceptable cure is achieved even under less favorable application conditions (low humidity, low temperature). For more details on plasticizers reference is made to the relevant literature of technical chemistry.
  • diurethanes which can be prepared, for example, by reacting diols having OH end groups with monofunctional isocyanates, by selecting the stoichiometry such that substantially all free OH groups react.
  • excess isocyanate can then be removed from the reaction mixture, for example, by distillation.
  • Another method for the preparation of diurethanes is the reaction of monofunctional alcohols with diisocyanates, where possible all of the NCO groups react.
  • the curable composition comprises at least one plasticizer, in particular a polydimethylsiloxane.
  • the curable compositions contain the reactive diluent, the solvent and / or the plasticizer preferably in an amount of 1 to 50 wt .-%, preferably in an amount of 10 to 40 wt .-%, particularly preferably in an amount of 20 to 30 wt .-%, each based on the total weight of the composition. If a mixture of a plurality of reactive diluents, solvents and / or plasticizers is used, the amounts given are of course based on the total amount of reactive diluents, solvents and / or plasticizers in the composition.
  • the curable composition contains at least one stabilizer selected from antioxidants, UV stabilizers and desiccants.
  • Antioxidants are all conventional antioxidants in question. They are preferably up to about 7 wt .-%, in particular up to about 5 wt .-% contained.
  • the composition herein may contain UV stabilizers, which are preferably used up to about 2% by weight, preferably about 1% by weight.
  • UV stabilizers are the so-called hindered amine light stabilizers (HALS).
  • HALS hindered amine light stabilizers
  • Particularly suitable for this purpose are the products Lowilite 75, Lowilite 77 (Great Lakes, USA). It is also possible to add benzotriazoles, benzophenones, benzoates, cyanoacrylates, acrylates, sterically hindered phenols, phosphorus and / or sulfur.
  • compositions with desiccant moisture to increase shelf-life.
  • Such an improvement in shelf life can be achieved, for example, by the use of desiccants.
  • Suitable drying agents are all compounds which react with water to form an inert group relative to the reactive groups present in the preparation, and in so doing undergo the smallest possible changes in their molecular weight.
  • the reactivity of the desiccants to moisture penetrated into the preparation must be higher than the reactivity of the groups of the silyl-group-bearing polymer of the invention present in the composition
  • Suitable drying agents are, for example, isocyanates.
  • silanes are used as drying agents.
  • vinylsilanes such as 3-vinylpropyltriethoxysilane
  • oximesilanes such as methyl-0,0 ' , 0 " -butan-2-one-trioximosilane or 0,0 ' , 0 " , 0 "' -butan-2-onetetraoximosilane (CAS No. 022984- 54-9 and 034206-40-1)
  • benzamidosilanes such as bis (N-methylbenzamido) methylethoxysilane (CAS No. 16230-35-6) or carbamatosilanes such as carbamatomethyltrimethoxysilane.
  • a desiccant are the abovementioned reactive diluents, provided that they have a molecular weight (M n ) of less than about 5,000 g / mol and end groups whose reactivity to moisture ingress is at least as great, preferably greater, than the reactivity of the reactive Groups of the polymer used according to the invention.
  • M n molecular weight
  • desiccants may also be alkyl orthoformates or orthoacetates, e.g. Methyl or ethyl orthoformate, methyl or ethyl orthoacetate,
  • compositions typically contain from about 0 to about 6 weight percent desiccant.
  • composition described herein may additionally contain fillers.
  • fillers For example, chalk, limestone, precipitated and / or fumed silica, zeolites, bentonites, magnesium carbonate, kieselguhr, clay, clay, talc, titanium oxide, iron oxide, zinc oxide, sand, quartz, flint, mica, glass powder and other ground minerals are suitable here.
  • organic fillers can be used, in particular carbon black, graphite, wood fibers, wood flour, sawdust, pulp, cotton, pulp, cotton, wood chips, chaff and chaff.
  • short fibers such as glass fiber, glass filament, polyacrylonitrile, carbon fiber, Kevlar fiber or even polyethylene fibers can be added.
  • Aluminum powder is also suitable as a filler.
  • the pyrogenic and / or precipitated silicas advantageously have a BET surface area of 10 to 90 m 2 / g. In their use, they do not cause an additional increase in the viscosity of the composition of the invention, but contribute to an enhancement of the cured composition.
  • pyrogenic and / or precipitated silicas having a higher BET surface area, advantageously from 100 to 250 m 2 / g, in particular from 1 to 170 m 2 / g, as filler. Due to the higher BET surface area, one can achieve the same effect, eg reinforcement of the cured preparation, at a lower weight proportion of silica. Thus, one can use other materials to improve the composition described herein in terms of other requirements.
  • hollow spheres with a mineral shell or a plastic shell are also suitable as fillers. These may be, for example, glass bubbles, which are commercially available under the trade names Glass Bubbles®.
  • Plastic-based hollow spheres, e.g. Expancel® or Dualite® are described, for example, in EP 0 520 426 B1. These are composed of inorganic or organic substances, each with a diameter of 1 mm or less, preferably of 500 ⁇ or less.
  • fillers are preferred which impart thixotropy to the formulations.
  • Such fillers are also described as rheological aids, e.g. As hydrogenated castor oil, fatty acid amides or swellable plastics such as PVC.
  • rheological aids e.g. As hydrogenated castor oil, fatty acid amides or swellable plastics such as PVC.
  • such preparations have a viscosity of 3,000 to 15,000, preferably 40,000 to 80,000 mPas or else 50,000 to 60,000 mPas.
  • the fillers are preferably used in an amount of 1 to 80 wt .-%, more preferably 2 to 20 wt .-%, and most preferably 5 to 10 wt .-%, each based on the total weight of the composition.
  • the amounts are based on the total amount of filler in the composition.
  • the preparation of the curable composition can be accomplished by simply mixing the polyorganosiloxane having at least one hydroxyl group attached to a silicon atom, the silane of formula (1), and optionally other ingredients. This can be done in suitable Dispersieraggregaten, z. As a high-speed mixer happen. Preferably, care is taken to ensure that the mixture does not come into contact with moisture where possible, which could lead to an undesirable premature curing. Corresponding measures are well known and include, for example, working in inert Atmosphere, such as under inert gas, and the drying / heating of individual components before they are mixed.
  • a preferred method of Herst II is to mix in a first step, the polyorganosiloxane having at least one hydroxyl group bonded to a silicon atom, and the silane of formula (1), wherein in the presence of at least one aminosilane and at least one plasticizer may, in a second step optionally add further ingredients with the exception of the curing catalyst and to mix all the ingredients, and finally in a third step to add a curing catalyst and to mix with the other ingredients.
  • the invention also relates to the use of the compositions of the invention as an adhesive, sealant or coating material.
  • composition or preparation can be used as an adhesive, sealant, putty and for the production of moldings. Another field of application of the compositions is the use as dowel, hole or putty.
  • compositions and preparations are therefore suitable for bonding plastics, metals, glass, ceramics, wood, wood-based materials, paper, paper materials, rubber and textiles, for bonding floors, sealing of structural parts, windows, wall and floor coverings and joints in general.
  • the materials can each be glued to each other or to each other.
  • the comparative composition VB1 was prepared.
  • polymer ( ⁇ , ⁇ -dihydroxy-terminated polydimethylsiloxane) and plasticizer with the curing agent vinyl tris (ethyllactato) silane and 3-aminopropyl-triethoxysilane were introduced and stirred for 5 min and then pulled for 5 min vacuum.
  • the fumed silica was added with stirring and the mixture was vacuumed.
  • the remaining aminosilanes and the catalyst were added and formulated under vacuum for 10 minutes.
  • the composition of the invention B2 was prepared.
  • a silane of the formula (1) was first prepared according to Example 1 from vinyl tris (ethyllactato) silane and 3-aminopropyltriethoxysilane and this without intermediate purification with polymer ( ⁇ , ⁇ -dihydroxy-terminated polydimethylsiloxane) and plasticizer and the mixture stirred for 5 min and then pulled for 5 min vacuum. Subsequently, the fumed silica was added with stirring and the mixture was vacuumed. Finally, the remaining aminosilanes and the catalyst were added and formulated under vacuum for 10 minutes.
  • the prepared formulations VB1 and B2 were examined for skin formation time, hardness, extensibility and elongation, as well as adhesion properties on various substrates. All tests were performed for the freshly formulated composition and after 4 and 12 weeks of aging at 40 ° C / 80% relative humidity.
  • the results for the comparative formulation VB1 are shown in Table 2, the results for the formulation B2 according to the invention in Table 3.
  • a comparison of the results for the comparative formulation VB1 and the inventive formulation B2 shows that an improved curing behavior (shorter skin formation times at comparable to slightly improved cure depths) can be achieved when using the silane according to the invention, and the mechanical properties of the cured product are comparable.
  • excellent adhesion (Cf1) can be consistently achieved for all the substrates investigated, while the comparison formulation shows weaknesses in the bonding of aluminum and wood.
  • GRP glass fiber reinforced plastic
  • GRP glass fiber reinforced plastic Measurement of skin formation time:
  • the skin formation time is determined in the normal climate (23 +/- 2 ° C, relative humidity 50 +/- 5%).
  • the temperature of the sealant must be 23 +/- 2 ° C, the sealant must be stored in the laboratory for at least 24 hours.
  • the sealant is applied to a sheet of paper and pulled out with a pulling spatula to a coat (thickness about 2 mm, width about 7 cm). Start the stopwatch immediately. At intervals, lightly touch the surface with your fingertip and pull your finger away - press so hard on the surface that an impression remains on the surface when skin formation time is reached. The skinning time is reached when no more sealant sticks to the fingertip. The skin formation time is given in minutes.
  • the procedure is carried out according to ISO 868.
  • a sealant strand with a height of 10 mm (+/- 1 mm) and a width of 20 mm (+/- 2 mm) is applied with a suitable spatula to a plastic card sheet.
  • a piece of the strand is cut out and the thickness of the hardened layer is measured with a caliper gauge. The hardening depth is given in [mm / 24 h].
  • the tensile test is used to determine the breaking force, elongation at break and elongation stress values (E-modules) in accordance with DIN 53504.
  • Deviation from the standard The test pieces used are shoulder bars with the following dimensions: Thickness: 2 +/- 0.2 mm; Width of the bridge: 10 +/- 0.5 mm; Length of the bridge: approx. 45 mm; Total length: 9 cm.
  • the test is carried out under standard conditions (23 +/- 2 ° C, 50 +/- 5% relative humidity). The test is carried out after 7 days of curing.
  • test specimens shall be clamped in the tensile tester in such a way that the longitudinal axis coincides with the mechanical axis of the tensile tester and the largest possible area of the rod ends is detected without pinching the web.
  • shoulder bar is tensioned to a preload of ⁇ 0.1 MPa. Then the force-length change curve is recorded at a feed rate of 50 mm / min.
  • Non-absorbent substrates are cleaned prior to application of the composition with a solvent mixture of acetone and isopropanol (mixing ratio 1: 3). Then 3 beads each (about 1.5 cm wide and about 3 mm thick) of the mass to be examined are applied to the substrate to be tested. The adhesion of the compound is assessed in each case after 2 weeks of pre-storage under standard conditions (23 ⁇ 2 ° C.) and (50 ⁇ 5% relative humidity). For this purpose, a bead is detached with a knife about 1 cm from the substrate. By pulling on this piece at an angle of approx. 90 ° an attempt is made to completely detach the bead. The breakage between sealant and substrate is assessed. A distinction is made between:

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PCT/EP2016/055693 2015-03-17 2016-03-16 Silane und härtbare zusammensetzungen, die diese silane als vernetzer enthalten WO2016146685A1 (de)

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CN201680016133.5A CN107428785B (zh) 2015-03-17 2016-03-16 硅烷和包含硅烷作为交联剂的可固化组合物
CA2979928A CA2979928C (en) 2015-03-17 2016-03-16 Silanes and curable compositions which contain said silanes as cross-linking agents
KR1020177029646A KR102572117B1 (ko) 2015-03-17 2016-03-16 실란 및 상기 실란을 가교제로서 함유하는 경화성 조성물
PL16711802T PL3271367T3 (pl) 2015-03-17 2016-03-16 Silany i kompozycje utwardzalne zawierające te silany jako czynniki sieciujące
JP2017549078A JP6688313B2 (ja) 2015-03-17 2016-03-16 シランおよび該シランを架橋剤として含有する硬化性組成物
BR112017019626-3A BR112017019626B1 (pt) 2015-03-17 2016-03-16 Silanos e composições endurecíveis que contém esses silanos comoreticulantes, e método para a fabricação de silanos
MX2017011821A MX2017011821A (es) 2015-03-17 2016-03-16 Silanos y composiciones curables que contienen dichos silanos como reticulantes.
ES16711802T ES2717522T3 (es) 2015-03-17 2016-03-16 Silanos y composiciones curables que contienen estos silanos como reticulantes
EP16711802.5A EP3271367B1 (de) 2015-03-17 2016-03-16 Silane und härtbare zusammensetzungen, die diese silane als vernetzer enthalten
RU2017134289A RU2711919C2 (ru) 2015-03-17 2016-03-16 Силаны и отверждаемые композиции, которые содержат эти силаны в качестве сшивающих агентов
US15/702,820 US10487096B2 (en) 2015-03-17 2017-09-13 Silanes and curable compositions containing said silanes as crosslinkers

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PL3660118T3 (pl) * 2018-11-30 2022-02-14 Henkel Ag & Co. Kgaa Utwardzalne kompozycje silikonowe zawierające dodatki
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EP3875541A1 (de) 2020-03-03 2021-09-08 PolyU GmbH Zusammensetzung und verfahren zur herstellung von silikonmassen und deren verwendung
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CN109790190B (zh) * 2016-07-13 2022-08-02 硝基化学阿绍有限公司 用于有机硅橡胶物料的固化剂
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JPWO2019069706A1 (ja) * 2017-10-06 2020-11-05 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物の製造方法、室温硬化性オルガノポリシロキサン組成物及び物品
WO2019219918A1 (en) * 2018-05-18 2019-11-21 Henkel Ag & Co. Kgaa Curable silicone compositions
KR20210010860A (ko) * 2018-05-18 2021-01-28 헨켈 아게 운트 코. 카게아아 경화성 실리콘 조성물
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WO2019219922A1 (en) * 2018-05-18 2019-11-21 Henkel Ag & Co. Kgaa Curable compositions comprising adhesion promoters
EP3569649A1 (en) * 2018-05-18 2019-11-20 Henkel AG & Co. KGaA Curable silicone compositions
US11753528B2 (en) 2018-05-18 2023-09-12 Henkel Ag & Co. Kgaa Endcapped curable polyorganosiloxanes
US11873386B2 (en) 2018-05-18 2024-01-16 Henkel Ag & Co. Kgaa Curable silicone compositions
KR102664516B1 (ko) 2018-05-18 2024-05-08 헨켈 아게 운트 코. 카게아아 경화성 실리콘 조성물
WO2020038950A1 (de) 2018-08-20 2020-02-27 Nitrochemie Aschau Gmbh Zusammensetzung für silikonkautschukmassen
EP3613803A1 (de) 2018-08-20 2020-02-26 Nitrochemie Aschau GmbH Zusammensetzung für silikonkautschukmassen

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CA2979928A1 (en) 2016-09-22
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US10487096B2 (en) 2019-11-26
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JP6688313B2 (ja) 2020-04-28
BR112017019626B1 (pt) 2021-02-23
EP3271367B1 (de) 2019-01-30
JP2018513129A (ja) 2018-05-24
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DE102015204788A1 (de) 2016-09-22
CN107428785B (zh) 2021-05-07
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KR102572117B1 (ko) 2023-08-30
CA2979928C (en) 2023-03-28
RU2017134289A (ru) 2019-04-03
BR112017019626A2 (pt) 2018-05-15
EP3271367A1 (de) 2018-01-24
RU2711919C2 (ru) 2020-01-24

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